Bostonian Ally Darling (Anna Faris) looks back at the past twenty men that she has had relationships with and wonders if one of them might be her true love. She enlists the help of her neighbor, Colin Shea (Chris Evans) in exchange to help him avoid his ex-girlfriends. Based on the Karyn Bosnak book "20 Times a Lady". Chris Pratt, Zachary Quinto, Joel McHale & Andy Samberg also star.